3,4-dihydro-2H-pyran → 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile

HRID 475207Notes

Reaction equation

HRID 475207 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178509527HCID 178509527, compound

Product 1

HCID 712723941-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrileYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 90 (1.63 g, 11.4 mmol), 3,4-dihydro-2H-pyran (2.87 g, 34.2 mmol), and p-TsOH.H2O (196 mg, 1.14 mmol) in THF (60 mL) was stirred under nitrogen at 80° C. for 18 h. The reaction mixture was concentrated in vacuo. The crude product was purified by SiO2 chromatography with eluting with petroleum ether/EtOAc (1:1) to afford 2.48 g (95.9%) of 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile (92) as yellow oil: MS (ESI) m/z=228.1 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude product was purified by SiO2 chromatography
  3. washwith eluting with petroleum ether/EtOAc (1:1)

Sources & evidence

ORD record
ord-f487ea6197644094aa90325432eecae1
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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